Buchwald–Hartwig amination, record ord-b3e000ca67494471adc7944fbfb45b78
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-(2-Chloro-5-fluoro-4-pyridinyl)-5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazole | C₁₃H₁₃ClFN₃ | |
| Reactant | tert-Butyl [(1R,3R)-3-carbamoylcyclohexyl]carbamate | C₁₂H₂₂N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Tetrakis(triphenylphosphine)palladium | C₇₂H₆₀P₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl N-[(1R,3R)-3-[[4-(5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate | C₂₅H₃₄FN₅O₃ | 84.39% |
Conditions
- Temperature
- 100 °C
Yield
- 84% of tert-butyl N-[(1R,3R)-3-[[4-(5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate.
Procedure
Copied from the source record, unedited
Tetrakis(triphenylphosphine)palladium(0) (0.094 g, 0.08 mmol) was added to Racemic tert-butyl ((1R,3R)-3-carbamoylcyclohexyl)carbamate (0.235 g, 0.97 mmol),3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.215 g, 0.81 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (0.094 g, 0.16 mmol) and cesium carbonate (0.791 g, 2.43 mmol) in 1,4-dioxane (6 mL) and water (1.200 mL). The resulting suspension was degassed for 10 minutes under nitrogen and then stirred at 100 °C for 48 hours. LCMS is complete, it needs this long. The mixture was cooled, diluted with water (40 ml), and extracted with EtOAc (3 x 20 ml). The combined organics were evaporated to crude material. The crude product was purified by flash silica chromatography, elution gradien
The source
This record comes from experimental reaction archive (ord-b3e000ca67494471adc7944fbfb45b78). Open the source and check it against what is on this page.
experimental reaction archive record ord-b3e000ca67494471adc7944fbfb45b78 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.